90786-23-5Relevant academic research and scientific papers
Sulphonamidomercuration; a New Method for Amination of Olefins
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
, p. 1178 - 1179 (1981)
The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkyl-sulphonamides; the use of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles, the synthesis of tosylated pyrrolidine being a stereoselective reaction.
Sulphonamidomercuriation of Olefins and Subsequent Reductive Demercuriation or Bromodemercuriation
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
, p. 721 - 725 (2007/10/02)
The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkylsulphonamides.The sulphonamidomercuriation-demercuriation of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles.A possible mechanism for the stereoselective synthesis of cis-2,5-dimethyl-N-tosylpyrrolidine is proposed.The treatment of the intermediate organomercurials, isolated as the sodium salts of their bromomercurio derivatives, with bromine gives the corresponding 2-bromoalkylsulphonamides through a regiospecific bromodemercuriation process.
